How to know if you are anentrepreneur

Things have really changed since I did my first startup back in 1986. Back then, if you told your parents that you wanted to be an entrepreneur it was like telling them that you were planning to be a rock star! Today is very different. We encourage, even push our young people into doing startups. It’s cool now to be an entrepreneur… maybe even too cool.

I am sometimes criticized for the first chapter of my book, The StartUp Hats. Some say it sounds like I’m trying to talk people out of becoming entrepreneurs. Just because you are smart and tenacious enough to be an entrepreneur does not mean that this career choice will make you happy and in my definition of success, if you miss “happy” then you have failed no matter how much money you make.

How do you know if you will be happy as an entrepreneur? I believe there are a few telling indicators that can give you a clue.

Are you Ok with messy?

One thing I can tell you with certainty is that a startup is often chaos. A bird only gets off the ground and flies if it flaps its wings feverishly. Some people thrive on such chaos. They enjoy the diversity of the day and struggling to slowly bring order to the mayhem. They aren’t overwhelmed by a need to get to the bottom of their in-box each day. If you need to have everything organized and in its proper place before you can call it a night, then the startup world is probably not for you. Successful entrepreneurs are always organizing. They keep a to-do list, but are perpetually reprioritizing it, demoting a handful of items, delegating some, and just doing enough to get by on others because that’s all the time they merit at the moment. This is more than multi-tasking. It’s making up rules and processes while you play. If you can’t get comfortable with chaos, entrepreneurship is probably going to kill you or at least leave you longing for that predictable corporate job you abandoned.

Are you OK with uncertainty?

Entrepreneurs thrive on being a little afraid. It gets them out of the bed and going each morning. That fear turns into energy and excitement. Starting a new venture is a rush. You put together a little pot of money against a plan that you honestly don’t know will work and then you try like hell to get cash flowing before your dollars run out. It’s like jumping out of an airplane without a parachute; all you have is a bag full of really ambitious silk worms and you are knitting as fast as you can all of the way down!

Does risk intrigue you or repel you? Are you happiest when everything is easily organized and in its place or when options are flying round with unlimited possibilities and potential? A life in the ranks can certainly offer more security and predictability but not what most would consider adventure. If the unknown and uncertain calls out to you then you might be an entrepreneur.

Are you OK with crazy hard work?

Besides being at peace with chaos, entrepreneurs are also known for their work ethic. Do you feel cheated after a hard day’s work that ran longer than expected and cut into your free time or do you arrive home with a feeling of extra accomplishment? Starting your own venture will probably be the most difficult thing you’ll ever do. You will work harder than you have ever worked, but if entrepreneurship runs in your veins then it won’t really feel like it does when you work hard for someone else. Another good definition of an entrepreneur is people who are so crazy that they will work seventy hours per week for themselves just so they don’t have to work forty for anyone else! When the line between your work and leisure starts to blur and you don’t really care then you might just be an entrepreneur.

Are you OK with sales?

With very few exceptions, the successful entrepreneurs I know have all made peace with the necessity of perpetually selling. Most of them really enjoy making their case and convincing others of the merits of their arguments. I’ve heard a lot of would-be entrepreneurs tell me, “I’m not a sales person.” To this I typically respond, “Then you are probably not an entrepreneur.”

There’s no getting around it, if you are starting a company then you are going to spend perhaps the largest part of your day under the sales hat. You are going to be selling investors on how your venture is going to make them a good return. You are going to be selling the best candidates on why they should work for your little startup. You are going to be selling those first few critically important prospects on why they should take a chance on you. When you screw up, you are going to be selling the customers you’ve disappointed on why they should continue to believe in you and give you another chance. Indeed, the sales hat is one you never truly get to hand off for very long. Even when your company grows to hundreds or even thousands of sales professionals, when the deal is big, the damage unthinkable or the account critical, you are going to be once again drafted into sales. So, if you just can’t see yourself doing the job of a sales person then find a partner who lives for it or seriously rethink your foray into entrepreneurship.

Are you OK with imperfect?

There is another personality type that I’ve seen struggle with entrepreneurship; the perfectionist. Startups are usually not the place where we have the opportunity to get things perfect or even try to do so. We generally do things just well enough and then move on. In other words, time is our most precious commodity so I encourage entrepreneurs to be very stingy with it. Since that last 10% often doubles the time commitment, it is usually not a good deal for entrepreneurs to get to perfect. They know that they could polish that PowerPoint® for another hour and perhaps make it 5% better, but this would be at the cost of not getting two other important tasks done that day. For most startups the goal is not perfection, but efficiency and good enough is almost always better than flawless in a startup. If that last sentence sticks in your claw then you may not be an entrepreneur.

So… are you an entrepreneur?

I met a successful executive at a party a while back. He seemed to know me and just started talking. I asked him if I had helped him with a venture. He said that we sat and talked on my back deck about ten years earlier and that I had helped him discover that he did not want to be an entrepreneur. He smiled, “Best advice I have ever received.”

My goal here is not to discourage entrepreneurship. In fact, I spend all day pretty much every day helping entrepreneurs achieve their dreams. Just keep in mind that not everyone will be happy in a startup so know yourself and make the life choices that feel right for you.